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Compound Detail

CHEMBL2158554

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COc1ccc(Nc2nc(-c3ccccc3)nc3ccccc23)cc1OC
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2158554
Phase Preclinical
Structure Type MOL
InChI Key LUUUIUBMYQYODQ-UHFFFAOYSA-N
3
Targets
11
Activities
1
Assay Types
0
PK Parameters
18
Publications
0
Known Names

Molecular Properties

357.4
MW (Da)
5.06
ALogP
5
HBA
1
HBD
56.3
PSA (Ų)
0.54
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H19N3O2
MW 357.41
Aromatic Rings 4
Heavy Atoms 27
NP-Likeness -1.23

Activity Summary

IC50 11 meas. best 6.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Broad substrate specificity ATP-binding cassette transporter ABCG2
CHEMBL5393
 IC50 6.82 6.62 152.0 5
ATP-dependent translocase ABCB1
CHEMBL4302
 IC50 5.73 5.355 1860.0 4
Multidrug resistance-associated protein 1
CHEMBL3004
 IC50 4.95 4.95 11180.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 152.0 nM 6.82 Inhibition of c-terminal GFP-tagged human ABCG2 expressed in MDCK2 cells preincu... 30075623
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 152.0 nM 6.82 Inhibition of GFP-fused human ABCG2 expressed in MDCK2 cells assessed as Hoechst... 30390439
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 152.0 nM 6.82 Inhibition of c-terminal GFP-tagged human ABCG2 expressed in MDCK2 cells preincu... 27148793
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 190.0 nM 6.72 Inhibition of human BCRP expressed in MDCK2 cells preincubated for 30 mins prior... 23017888
Broad substrate specificity ATP-binding cassette transporter ABCG2 IC50 = 1190.0 nM 5.92 Inhibition of BCRP (unknown origin) expressed in MDCK cells assessed as increase... 29016119
ATP-dependent translocase ABCB1 IC50 = 1860.0 nM 5.73 Inhibition of ABCB1 in human A2780adr cells preincubated for 30 mins before calc... 27148793
ATP-dependent translocase ABCB1 IC50 = 5850.0 nM 5.23 Inhibition of human P-gp overexpressed in doxorubicin resistant A2780adr cells p... 23017888
ATP-dependent translocase ABCB1 IC50 = 5850.0 nM 5.23 Inhibition of MDR1 in human doxorubicin-resistant A2780adr cells assessed as Cal... 24184213
ATP-dependent translocase ABCB1 IC50 = 5850.0 nM 5.23 Inhibition of P-gp (unknown origin) expressed in human A2780 ADR cells by calcei... 29016119
Multidrug resistance-associated protein 1 IC50 = 11180.0 nM 4.95 Inhibition of human MRP1 expressed in 2008 cells preincubated for 30 mins prior ... 23017888
Multidrug resistance-associated protein 1 IC50 = 11180.0 nM 4.95 Inhibition of MRP1 in human 2008 cells assessed as Calcein AM accumulation treat... 24184213

Literature References

PubMed DOI Target Context # Activities
30390439 10.1016/j.ejmech.2018.10.026 Broad substrate specificity ATP-binding cassette transporter ABCG2 3
23017888 10.1016/j.bmcl.2012.08.024 ATP-dependent translocase ABCB1 2
23017888 10.1016/j.bmcl.2012.08.024 Multidrug resistance-associated protein 1 2
30075623 10.1021/acs.jmedchem.8b01011 MDCK-II 2
27148793 10.1021/acs.jmedchem.6b00330 MDCK-II 2
27148793 10.1021/acs.jmedchem.6b00330 ATP-dependent translocase ABCB1 2
27148793 10.1021/acs.jmedchem.6b00330 Broad substrate specificity ATP-binding cassette transporter ABCG2 2
29016119 10.1021/acs.jmedchem.7b00788 Broad substrate specificity ATP-binding cassette transporter ABCG2 1
29016119 10.1021/acs.jmedchem.7b00788 ATP-dependent translocase ABCB1 1
27148793 10.1021/acs.jmedchem.6b00330 ADMET 1
27148793 10.1021/acs.jmedchem.6b00330 Multidrug resistance-associated protein 1 1
30075623 10.1021/acs.jmedchem.8b01011 ADMET 1
30075623 10.1021/acs.jmedchem.8b01011 Broad substrate specificity ATP-binding cassette transporter ABCG2 1
30075623 10.1021/acs.jmedchem.8b01011 ATP-dependent translocase ABCB1 1
30075623 10.1021/acs.jmedchem.8b01011 Multidrug resistance-associated protein 1 1
24184213 10.1016/j.bmc.2013.10.007 ATP-dependent translocase ABCB1 1
24184213 10.1016/j.bmc.2013.10.007 Multidrug resistance-associated protein 1 1
23017888 10.1016/j.bmcl.2012.08.024 Broad substrate specificity ATP-binding cassette transporter ABCG2 1

Data from ChEMBL 36 via Core Engine